Liquid conductivity additives for nonaqueous hydraulic oils

ABSTRACT

Composition comprising nonaqueous hydraulic oils or lubricants and one or more conductivity additives which form clear solutions or mixtures with the hydraulic oil and optionally further customary additives for increasing the conductivity of nonaqueous hydraulic oils and/or lubricants.

This application claims benefit under 35 U.S.C. 119(a) of German patentapplication 10 2008 001 674.8, filed on 9 May 2008.

Any foregoing applications, including German patent application DE 102008 001 674.8, and all documents cited therein or during theirprosecution (“application cited documents”) and all documents cited orreferenced in the application cited documents, and all documents citedor referenced herein (“herein cited documents”), and all documents citedor referenced in herein cited documents, together with anymanufacturer's instructions, descriptions, product specifications, andproduct sheets for any products mentioned herein or in any documentincorporated by reference herein, are hereby incorporated herein byreference, and may be employed in the practice of the invention.

Hydraulic oils serve for power transmission in machines. A pump conveysoil through a conduit, at the end of which a piston is moved by thehydraulic oil. On the basis of the lever principle, it is thus possibleto transmit large forces with comparatively low pump power.

According to the end use and required property, hydraulic fluids are ofdifferent structure. The liquids are divided according to ISO 6743 intomineral oil-based, low-flammability and environmentally friendly fluids.

The most frequently used hydraulic fluids, but also lubricants, arebased on mineral oils with appropriate additives. They are also referredto as hydraulic oils. The requirements on these hydraulic oils are laiddown in ISO 6743/4 with the designations HL, HM, HV. In Germany, thedesignations HL, HLP, HVLP according to DIN 51524 are customary.

[HL: comprising active ingredients to increase corrosion protection andageing stability (including HL to DIN 51524, part 1); HM: comprisingactive ingredients to increase corrosion protection and ageingstability, and to reduce scuffing in the mixed friction range (includingHLP to DIN 51524, part 2); HV: comprising active ingredients to increasecorrosion protection and ageing stability, and to reduce scuffing in themixed friction range and to improve the viscosity-temperature behaviour(including HVLP DIN 51524, part 3)].

Additionally of significance are anhydrous, synthetic, nonflammablefluids. They are based on the following compounds:

-   -   phosphoric esters (HFD R), nowadays the most frequently used HFD        fluid; but has the lowest nonflammability,    -   chlorinated hydrocarbons (HFD S); for reasons of environmental        protection, now used only in closed systems for coal mining,    -   mixtures of HFD R and HFD S,    -   other compositions (HFD U).

In addition, biodegradable hydraulic fluids based on vegetable oils(e.g. based on rape) are being produced and used in biologicallycritical environments (construction machinery in water protection areas,piste machinery in mountains, etc.). These fluids are pollutants inGerman Schadstoffklasse I and are abbreviated to: HE=HydraulicEnvironmental. The individual substance classes are subdivided asfollows:

-   -   HETG (based on triglycerides=vegetable oils),    -   HEES (based on synthetic esters),    -   HEPG (based on polyglycols)    -   HEPR (other base fluids, primarily poly-alpha-olefins).

Manufacturers of hydraulic equipment require predominantly products toDIN 51524 part 2 “HLP” or part 3 “HVLP”. Oils of this quality mustpossess a particular water separation capacity, filterability, sealcompatibility, air separation capacity, oxidation stability, wearprotection, etc. (Some parts of DIN 51524 have been revised in 2005. Thenew version of DIN 51524 was published in April 2005. The significantchange is the newly introduced 21/19/16 purity class).

The general assessment of a hydraulic overall system in relation toeconomic viability, reliability, low maintenance costs and high machineavailability is influenced by the use of high-grade components, forexample valves, control pumps, lubricant and hydraulic media.

Ultrafine particles considerably influence the lifetime of a hydraulicsystem through abrasion and other undesired side effects. For thisreason, the manufacturers of hydraulic systems stipulate that the oilshould be filled into the system through special filters.

In the analysis of damage to hydraulic and lubricant systems, damage tothe components used, caused by hard solid particles which occur in highconcentration in the operating medium, are usually diagnosed as thecause.

The intensity of component damage as a result of solid contamination inthe lubricant and hydraulic oil depends on

-   -   material of the contamination (the harder the particles are, the        greater is the component damage)    -   operating pressure (the higher the operating pressure, the more        strongly the solid particles are forced into the lubricated        gap).

The failure of hydraulic and lubricant components can usually beattributed to the following causes:

-   -   coarse particles (>15 μm): sudden component failure,    -   fine contamination (5-15 μm): component wear, leaks, valve        blockages,    -   ultrafine contamination (<2-5 μm): sludge accumulation in the        oil, relatively rapid oil ageing.

The filters used in lubricant and hydraulic systems have the task ofensuring compliance with the solids contamination limits. In order thatthis aim can be achieved, these filters must be mounted very close tothe soil introduction site, must have the necessary filter fineness, andmust be installed within the largest volume flow, in order that a hightank circulation is achieved. If possible, the system filtration shouldbe supported by effective tank circulation (secondary flow filtration).

In order that damage to the filter element is prevented, and aneconomically viable, cost-optimized element changeover is possible, thefilter should be provided with an active contamination indicator which,if ignored, shuts down the system.

These recommendations should have the effect that the component lifetimerequired by the operator and hence the service life of the overallsystem can be satisfied. The task of the hydraulic filters used in thesystem and of the correct positioning thereof in the system is toimplement and comply with these purity class requirements over theentire service life of the system. In the case of new oils inparticular, which are supplied in vats, tankers or minicontainers,inadmissibly high solid contamination is to be expected.

The use of high-grade filters with elements which, in the multipass testto ISO 16889, display particle separation over a wide particle sizerange, have a high soil absorption, and guarantee a low pressuredifference at the filter element and housing, a high collapse andbursting pressure resistance and a high dynamic pressure and volume flowpulsation resistance, noticeably reduces the concentration of the solidcontamination in lubricant and hydraulic media, with the aim ofpreventing premature component failure. A low solid concentration in theindividual particle sizes in the lubricant and hydraulic media is theprerequisite for the entire system being operable economically andreliably.

In the filtration processes, especially at low ambient temperatures, asexist, for example, in cold stores, charge separations occur, which leadto static charging.

The lower the temperature, the greater the problem of static charging,especially also at reduced air humidity and/or residual moisture contentin closed systems.

Spark formation, which is possible as a result of static charging,constitutes a high safety risk. To prevent this problem, conductivityadditives are needed, which ensure a minimum conductivity of thehydraulic fluid and thus ensure discharge. Typically, solid salts areused in conjunction with organic solvents. The latter are needed inorder to achieve at least a minimum solubility. This configuration hasvarious disadvantages. Firstly, the organic solvents increase theflammability and the combustibility of the hydraulic fluid; secondly,they are volatile and constitute a safety risk. Furthermore, thevolatility has the effect that the solubility of the conductive saltsdecreases and they are filtered out with time and can even lead todamage to the hydraulic system as a result of friction. In addition, thehydraulic fluid thus loses its antistatic modification. In conjunctionwith the organic solvents still present in small amounts, theflammability and hence the safety risk increase as a consequence.

The maximum concentration of conductivity improver is thus limited, andhence also the maximum achievable conductivity of the hydraulic oils orlubricants.

In the context of this application, conductivity improvers are alsoreferred to as conductivity additives, though both terms should beconsidered as synonymous with one another.

It is therefore an object of the present invention to overcome theindicated shortcomings in the prior art and to provide novelconductivity improvers which are capable of ensuring lasting antistaticmodification of hydraulic oils and/or lubricants.

Surprisingly, liquid conductivity additives have now been found, whichare soluble in the nonaqueous hydraulic fluid and/or the lubricant or atleast form clear mixtures with the hydraulic fluid and/or the lubricantand can be used advantageously in hydraulic oils and/or lubricants.

These liquid conductivity additives contain ions with organic radicalsand have very low vapour pressures and hence also low volatilities.

The invention therefore provides compositions comprising nonaqueoushydraulic oils or lubricants and one or more liquid conductivityadditives which contain organic ions and may optionally contain furthercustomary additives.

Preference is given to compositions which comprise liquid ionicconductivity additives in which at least either the cation and/or theanion has/have organic radicals.

Particular preference is given to compositions which comprise ionicconductivity additives which have at least one cation and/or anion withorganic radicals.

The ionic conductivity additive preferably contains, in the cationand/or anion, at least one organic radical having at least eight carbonatoms, where the sum of the carbon atoms of all radicals is at least 14.

Particular preference is given to ionic conductivity additives with atleast one radical in the cation and/or anion which contains at least 12carbon atoms, where the sum of the carbon atoms of all radicals is atleast 22.

Very particular preference is given to conductivity additives with twoor more organic radicals in the cation and/or anion which contain atleast 12 carbon atoms and in which the sum of all radicals is at least26.

The invention further provides for the use of liquid organicconductivity additives in hydraulic or lubricant systems, especially inthose in which the lubricant is filtered continuously orsemicontinuously, especially at temperatures between +20° C. and −75°C., preferably between +10° C. and −50° C., more preferably between 5°C. and −25° C. Useful lubricant systems include lubricant systems intwo-stroke engines, gasoline engines and diesel engines, automatictransmission, manual transmission, brake circuits, hydraulic systems,air and gas compressors, gearboxes, ball bearings, gas turbines, steamturbines, cooling circuits, which are used, for example, in automobiles,trucks, tractors, aircraft, ships and industrial systems. Preferredlubricant systems are hydraulic systems; particular preference is givento hydraulic systems which are filtered continuously.

The use of the inventive compositions allows the conductivity of thehydraulic oils to be increased and hence the hazard potential ofelectrical charging to be avoided; in addition, the required propertiesof the hydraulic oils with regard to vapour pressure/volatility,flammability, filtration capacity, turbidity and stability of theformulation are improved, but at least not adversely affected.

It is especially advantageous that the conductivity additive is liquidand does not separate out of the formulation in crystalline form, whichcan lead to the described problems with conventional additives when theyare used in hydraulic or lubricant systems.

The conductivity additives used in accordance with the invention arecomposed preferably of at least one cation [A⁺], corresponding to aquaternary nitrogen compound and/or phosphorus compound and/or sulphurcompound and at least one anion, and their melting point is below about+250° C., preferably below approx. +150° C., especially below approx.+100° C. The conductivity additives used in accordance with theinvention or mixtures thereof are more preferably liquid at roomtemperature, preferably at the use temperatures.

A further advantage of the inventive formulations is that they, as aresult of the increased solubility of the inventive conductivityadditives, can also be used at temperatures below room temperature, evensignificantly below freezing point.

It is thus also possible at low temperatures to increase conductivityand counter static charge, especially in the course of filtration.

In the context of the present invention, conductivity additives aresalts of the general formulae (I), (II) and (III) listed below:

[A] _(n) ⁺[Y]^(n−)  (I)

in which

-   n is 1, 2, 3 or 4,-   [A]⁺ is a quaternary ammonium cation, an oxonium cation, a    sulphonium cation or a phosphonium cation and-   [Y]^(n−) is an n-valent anion and/or mixed salts of the general    formula (II)

[A¹]⁺[A²]⁺[Y]²⁻  (IIa)

[A¹]⁺[A²]⁺[A³]⁺[Y]³⁻  (IIb) or

[A¹]⁺[A²]⁺[A³]⁺[A⁴]⁺[Y]⁴⁻  (IIc)

where

-   [A¹]⁺, [A²]⁺ [A³]⁺ and [A⁴]⁺ are each independently selected from    the groups specified for [A]⁺ 0 and [Y]^(n−) is as defined for    formula (I) and/or mixed salts of the general formulae (III)

[A¹]⁺[A²]⁺[A³]⁺[M¹]⁺[Y]⁴⁻  (IIIa)

[A¹]⁺[A²]⁺[M¹]⁺[M²]⁺[Y]⁴⁻  (IIIb)

[A¹]⁺[M¹]⁺[M²]⁺[M³]⁺[Y]⁴⁻  (IIIc)

[A¹]⁺[A²]⁺[M¹]⁺[Y]³⁻  (IIId)

[A¹]⁺[M¹]⁺[M²]⁺[Y]³⁻  (IIIe)

[A¹]⁺[M¹]⁺[Y]²⁻  (IIIf)

[A¹]⁺[A²]⁺[M⁴]²⁺[Y]⁴⁻  (IIIg)

[A¹]⁺[M¹]⁺[M⁴]²⁺[Y]⁴⁻  (IIIh)

[A¹]⁺[M⁵]³⁺[Y]⁴⁻  (IIIi) or

[A¹]⁺[M⁴]²⁺[Y]³⁻  (IIIj)

where

-   [A¹]⁺, [A²]⁺ or [A³]⁺ are each independently selected from the    groups specified for [A]⁺,-   [Y]^(n−) is as defined for formula (I) and-   [M¹]⁺, [M²]⁺, [M³]⁺ are each monovalent metal cations,-   [M⁴]²⁺ are divalent metal cations and-   [M⁵]³⁺ are trivalent metal cations, or mixtures of all formulae (I)    to (III).

The metal cations [M¹]⁺, [M²]⁺, [M³]⁺, [M⁴]²⁺ and [M⁵]³⁺ specified inthe formulae (IIIa) to (IIIj) are generally metal cations of groups 1,2, 6, 7, 8, 9, 10, 11, 12 and 13 of the Periodic Table in the IUPACnomenclature. Suitable metal cations are, for example, Li⁺, Na⁺, K⁺,Cs⁺, Mg²⁺, Ca²⁺, Ba²⁺, Cr³⁺, Fe²⁺, Fe³⁺, Co²⁺, Ni²⁺, Cu²⁺, Ag⁺, Zn²⁺ andAl³⁺.

The inventive conductivity additives consist of anions, for examplehalides, carboxylates, phosphates, thiocyanates, isothiocyanates,dicyanamides, sulphates, alkylsulphates, sulphonates, alkylsulphonates,tetra-fluoroborate, hexafluorophosphate or elsebis(trifluoromethylsulphonyl)imide, combined with, for example,substituted ammonium, phosphonium, pyridinium or imidazolium cations,where the aforementioned anions and cations constitute a small selectionfrom the large number of possible anions and cations and hence are notintended to make any claim of completeness or even impose a restriction.

The conductivity additives which are used with preference in the contextof the invention may consist, for example, of at least one organiccation [A⁺] of the general formulae

R¹R²R³R⁴N⁺  (IV)

R¹R²N⁺═CR³R⁴  (V)

R¹R²R³R⁴P⁺  (VI)

R¹R²P⁺═CR³R⁴  (VII)

R¹R²R³S⁺  (VIII)

in which

-   R¹, R², R³, R⁴ are the same or different with the proviso that at    least one radical is not hydrogen, and are each hydrogen, a linear    or branched aliphatic hydrocarbon radical which has 1 to 30 carbon    atoms and may contain double bonds, a cycloaliphatic hydrocarbon    radical which has 5 to 40 carbon atoms and may contain double bonds,    an aromatic hydrocarbon radical having 6 to 40 carbon atoms, an    alkylaryl radical having 7 to 40 carbon atoms, a linear or branched    aliphatic hydrocarbon radical which has 2 to 30 carbon atoms, may    contain double bonds and is interrupted by one or more heteroatoms    (oxygen, NH, NR′ where R′ is a C₁-C₃₀-alkyl radical which may    contain double bonds, especially —CH₃), a linear or branched    aliphatic hydrocarbon radical which has 2 to 30 carbon atoms, may    contain double bonds and is interrupted by one or more    functionalities selected from the group of —O—C(O)—, —(O)C—O—,    —NH—C(O)—, —(O)C—NH, —(CH₃)N—C(O)—, —(O)C—N(CH₃)—, —S(O₂)—O—,    —O—S(O₂)—, —S(O₂)—NH—, —NH—S(O₂)—, —S(O₂)—N(CH₃)—, —N(CH₃)—S(O₂)—, a    linear or branched aliphatic or cycloaliphatic hydrocarbon radical    which has 1 to 30 carbon atoms, may contain double bonds and is    functionalized terminally with OH, OR′, NH₂, N(H)R′, N(R′)₂ in which    R′ is a C₁-C₃₀-alkyl radical which may contain double bonds, or a    polyether of blockwise or random construction according to    —(R⁵—O)_(n)—R⁶,    where-   R⁵ is a linear or branched hydrocarbon radical containing 2 to 4    carbon atoms,-   n is 1 to 100, preferably 2 to 60, and-   R⁶ is hydrogen, a linear or branched aliphatic hydrocarbon radical    which has 1 to 30 carbon atoms and may contain double bonds, a    cycloaliphatic hydrocarbon radical which has 5 to 40 carbon atoms    and may contain double bonds, an aromatic hydrocarbon radical having    6 to 40 carbon atoms, an alkylaryl radical having 7 to 40 carbon    atoms or a —C(O)—R⁷ radical where-   R⁷ is a linear or branched aliphatic hydrocarbon radical which has 1    to 30 carbon atoms and may contain double bonds, a cycloaliphatic    hydrocarbon radical which has 5 to 40 carbon atoms and may contain    double bonds, an aromatic hydrocarbon radical having 6 to 40 carbon    atoms, an alkylaryl radical having 7 to 40 carbon atoms.

Preference is given to quaternary ammonium salts of alkoxylated fattyacids—also referred to as alkanolamine ester quats—characterized by thegeneric formula of the R¹R²R³R⁴N⁺ A⁻ (IV) type in which R¹ is an alkylradical having 1 to 20 carbon atoms, R² is an alkyl radical having 1 to4 carbon atoms, R³ is a (CH₂CHRO)_(n)—H radical where n is 1 to 200 andR is H or CH₃, R⁴ is an alkyl radical having 1 to 4 carbon atoms or a(CH₂CHRO)_(n)—H radical where n is 1 to 200 and R is H or CH₃, and A⁻ isa monovalent anion.

Among these compounds, preference is given to substances of the formula

R⁶ _(4-m)N⁺[(CH₂)_(n)-Q-R⁷]_(m) X⁻  (i)

where

-   each R⁶ radical is independently an alkyl group or hydroxyalkyl    group having 1 to 6 carbon atoms, or a benzyl group and preferably a    methyl group,-   R⁷ is independently hydrogen, a linear or branched alkyl group    having 11 to 22 carbon atoms, a linear or branched alkenyl group    having 11 to 22 carbon atoms, with the condition that at least one    R⁷ radical is not hydrogen,-   Q is independently selected from the groups of the formulae —O—C    O)—, —C(O)O, —NR⁸—C(O)—, —C(O)—NR⁸—, —O—C(O)—O, —CHR⁹—O—C(O)— or    —CH(OCOR⁷)—CH₂—O—C(O)—, where R⁸ is hydrogen or a methyl, ethyl,    propyl or butyl radical and R⁹ is hydrogen or methyl, and Q is    preferably —O—C(O)— or —NH—C(O)—;-   M is 1 to 4 and preferably 2 or 3;-   N is 1 to 4 and preferably 2; and-   X is an anion compatible with hydraulic oils, for example    methylsulphate, ethyl sulphate, methylsulphonate, butylsulphate,    octylsulphate, phosphinate or 2-(2-methoxyethoxy)ethylsulphate,    preferably methylsulphate, 2-(2-methoxyethoxy)ethylsulphate,    octylsulphate and phosphinate. The quaternary ammonium compound may    comprise mixtures of the compounds with different R⁷ groups which    are not hydrogen, the value of which ranges from 1 up to m. Such    mixtures preferably contain an average of 1.2 to 2.5 R⁷ groups which    are not hydrogen. The proportion of non-hydrogen R⁷ groups is    preferably 1.4 to 2.0 and preferentially 1.6 to 1.9.

The preferred quaternary ammonium compounds are the compounds of thetype:

R⁶N⁺[CH₂CHR⁹OH—][CH₂CHR⁹OC(O)R⁷]₂ X⁻  (ii)

R⁶N⁺[CH₂CHR⁹OC(O)R⁷]₂ X⁻  (iii)

R⁶N⁺[CH₂CHR⁹OH—][CH₂CH₂NHC(O)R⁷]₂ X⁻  (iv)

where R⁶, R⁷ and X are each as defined for formula (i) above, with thecondition that R⁷ is not hydrogen.

The —C(O)R⁷ fragment is preferably a fat-containing acyl group. Usablefat-containing acyl groups are derived from the natural sources of thetriglycerides, preferably tallow, vegetable oils, partially hydrogenatedtallow and partially hydrogenated vegetable oils. Usable sources of thetriglycerides are soybean oil, tallow, partially hydrogenated tallow,palm oil, palm kernels, rapeseeds, porcine fat, coconut, rape, saffloweroil, maize, rice and tall oil, and mixtures of these components.

The person skilled in the art is aware that the composition of the fattyacid-containing compounds is subject to certain natural variations, as afunction of the harvest or of the multitude of vegetable oil sources.The R⁷ groups are usually mixtures of the linear and branched carbonchains of the saturated and unsaturated aliphatic fatty acids.

The proportion of the unsaturated R⁷ groups in such mixtures ispreferably at least 10%, more preferably at least 25% and mostpreferably 40% to 70%. The proportion of the polyunsaturated R⁷ groupsin such mixtures is less than 10%, preferably less than 5% and morepreferably less than 3%. If required, partial hydrogenation can becarried out, in order to raise the saturated character and hence toimprove the stability (e.g. odour, colour, etc.) of the end product. Thecontent of unsaturated fractions, expressed by the iodine number, shouldbe within a range of 5 to 150 and preferably within a range ofpreferably 5 to 50. The ratio of cis and trans isomers of the doublebonds in the unsaturated R⁷ groups is preferably greater than 1:1 andmore preferably in the range of 4:1 to 50:1.

Preferred examples of the compounds of formula (i) are:

-   N,N-di(tallowyloxyethyl)-N,N-dimethylammonium chloride;-   N,N-di(canolyloxyethyl)-N,N-dimethylammonium chloride;-   N,N-di(tallowyloxyethyl)-N-methyl,N-(2-hydroxyethyl)-ammonium    methylsulphate;-   N,N-di(canolyloxyethyl)-N-methyl,N-(2-hydroxyethyl)-ammonium    methylsulphate;-   N,N-di(tallowylamidoethyl)-N-methyl,N-(2-hydroxyethyl)-ammonium    methylsulphate;-   N,N-di(2-tallowyloxy-2-oxo-ethyl)-N,N-dimethylammonium chloride;-   N,N-di(2-canolyloxy-2-oxo-ethyl)-N,N-dimethylammonium chloride;-   N,N-di(2-tallowyloxyethylcarbonyloxyethyl)-N,N-dimethylammonium    chloride;-   N,N-di(2-canolyloxyethylcarbonyloxyethyl)-N,N-dimethylammonium    chloride;-   N(2-tallowoyloxy-2-ethyl)-N-(2-tallowyloxy-2-oxo-ethyl)-N,N-dimethylammonium    chloride;-   N(2-canolyloxy-2-ethyl)-N(2-canolyloxy-2-oxo-ethyl)-N,N-dimethylammonium    chloride;-   N,N,N-tri(tallowyloxyethyl)-N-methylammonium chloride;-   N,N,N-tri(canolyloxyethyl)-N-methylammonium chloride;-   1,2-ditallowyloxy-3-N,N,N-trimethylammoniopropyl chloride; and-   1,2-dicanolyloxy-3-N,N,N-trimethylammoniopropyl chloride.

Further preferred quaternary ammonium salts are ditallowdimethylammoniumchloride, ditallowdimethylammonium methylsulphate, dimethylammoniumchloride of di(hydrogenated tallow) distearyldimethylammonium chlorideand dibehenyldimethylammonium chloride.

Useful cations are also ions which derive from saturated or unsaturatedcyclic compounds and from aromatic compounds having in each case atleast one trivalent nitrogen atom in a 4- to 10-membered, preferably 5-to 6-membered, heterocyclic ring which may optionally be substituted.Such cations can be described in simplified form (i.e. without astatement of the exact position and number of double bonds in themolecule) by the general formulae (IX), (X) and (XI) below, where theheterocyclic rings may optionally also contain a plurality ofheteroatoms such as nitrogen, oxygen or sulphur

-   where R¹ and R² are each as defined above,-   R is a hydrogen, a linear or branched aliphatic hydrocarbon radical    which has 1 to 30 carbon atoms and may contain double bonds, a    cycloaliphatic hydrocarbon radical which has 5 to 40 carbon atoms    and may contain double bonds, an aromatic hydrocarbon radical having    6 to 40 carbon atoms or an alkylaryl radical having 7 to 40 carbon    atoms, and-   X is an oxygen atom, a sulphur atom or a substituted nitrogen atom    (X=O, S, NR¹).

Examples of cyclic nitrogen compounds of the aforementioned type arepyrrolidine, dihydropyrrole, pyrrole, imidazoline, oxazoline, oxazole,thiazoline, thiazole, isoxazole, isothiazole, indole, carbazole,piperidine, pyridine, the isomeric picolines and lutidines, quinolineand isoquinoline. The cyclic nitrogen compounds of the general formulae(IX), (X) and (XI) may be unsubstituted (R=H), monosubstituted or elsepolysubstituted by the R radical, where, in the case of polysubstitutionby R, the individual R radicals may be the same or different.

Useful cations also include ions which derive from saturated acyclic,saturated or unsaturated cyclic compounds and from aromatic compoundshaving in each case more than one trivalent nitrogen atom in a 4- to10-membered, preferably 5- to 6-membered, heterocyclic ring. Thesecompounds may be substituted both on the carbon atoms and on thenitrogen atoms. They may also be fused by optionally substituted benzenerings and/or cyclohexane rings to form polycyclic structures. Examplesof such compounds are pyrazole, 3,5-dimethylpyrazole, imidazole,benzimidazole, N-methyl imidazole, dihydropyrazole, pyrazolidine,pyridazine, pyrimidine, pyrazine, 2,3-, 2,5- and 2,6-dimethylpyrazine,cinnoline, phthalazine, quinazoline, phenazine and piperazine.Especially cations derived from imidazole and the alkyl and phenylderivatives thereof can be used.

Useful cations are also ions which contain two nitrogen atoms and arerepresented by the general formula (XII)

in which

-   R⁸, R⁹, R¹⁰, R¹¹, R¹² are the same or different and are each    hydrogen, a linear or branched aliphatic hydrocarbon radical which    has 1 to 30 carbon atoms and may contain double bonds, a    cycloaliphatic hydrocarbon radical which has 5 to 40 carbon atoms    and may contain double bonds, an aromatic hydrocarbon radical having    6 to 40 carbon atoms, an alkylaryl radical having 7 to 40 carbon    atoms, a linear or branched aliphatic hydrocarbon radical which has    1 to 30 carbon atoms, may contain double bonds and is interrupted by    one or more heteroatoms (oxygen, NH, NR′ where R′ is a C₁-C₃₀-alkyl    radical which may contain double bonds), a linear or branched    aliphatic hydrocarbon radical which has 1 to 30 carbon atoms, may    contain double bonds and is interrupted by one or more    functionalities, selected from the group of —O—C(O)—, —(O)C—O—,    —NH—C(O)—, —(O)C—NH, —(CH₃)N—C(O)—, —(O)C—N(CH₃)—, —S(O₂)—O—,    —O—S(O₂)—, —S(O₂)—NH—, —NH—S(O₂)—, —S(O₂)—N(CH₃)—, —N(CH₃)—S(O₂)—, a    linear or branched aliphatic or cycloaliphatic hydrocarbon radical    which has 1 to 30 carbon atoms, may contain double bonds and is    functionalized terminally with OH, OR′, NH₂, N(H)R′, N(R′)₂ where R′    is a C₁-C₃₀-alkyl radical which may contain double bonds, or a    polyether of blockwise or random structure formed from    —(R⁵—O)_(n)—R⁶,    where-   R⁵ is a hydrocarbon radical containing 2 to 4 carbon atoms,-   n is 1 to 100 and-   R⁶ is hydrogen, a linear or branched aliphatic hydrocarbon radical    which has 1 to 30 carbon atoms and may contain double bonds, a    cycloaliphatic hydrocarbon radical which has 5 to 40 carbon atoms    and may contain double bonds, an aromatic hydrocarbon radical having    6 to 40 carbon atoms, an alkylaryl radical having 7 to 40 carbon    atoms or a —C(O)—R⁷ radical where-   R⁷ is a linear or branched aliphatic hydrocarbon radical which has 1    to 30 carbon atoms and may contain double bonds, a cycloaliphatic    hydrocarbon radical which has 5 to 40 carbon atoms and may contain    double bonds, an aromatic hydrocarbon radical having 6 to 40 carbon    atoms, an alkylaryl radical having 7 to 40 carbon atoms.

Very particularly preferred imidazolium ions (XII) include1-(1-octyl)imidazolium, 1-(1-dodecyl)imidazolium,1-(1-tetradecyl)imidazolium, 1-(1-hexadecyl)imidazolium,1-(1-butyl)-3-methylimidazolium, 1-(1-butyl)-3-ethylimidazolium,1-(1-hexyl)-3-methylimidazolium, 1-(1-hexyl)-3-ethylimidazolium,1-(1-hexyl)-3-butylimidazolium, 1-(1-octyl)-3-methylimidazolium,1-(1-octyl)-3-ethylimidazolium, 1-(1-octyl)-3-butylimidazolium,1-(1-dodecyl)-3-methylimidazolium, 1-(1-dodecyl)-3-ethylimidazolium,1-(1-dodecyl)-3-butylimidazolium, 1-(1-dodecyl)-3-octylimidazolium,1-(1-tetradecyl)-3-methylimidazolium,1-(1-tetradecyl)-3-ethylimidazolium,1-(1-tetradecyl)-3-butylimidazolium,1-(1-tetradecyl)-3-octylimidazolium,1-(1-hexadecyl)-3-methylimidazolium, 1-(1-hexadecyl)-3-ethylimidazolium,1-(1-hexadecyl)-3-butylimidazolium, 1-(1-hexadecyl)-3-octylimidazolium,1-(1-butyl)-2,3-dimethylimidazolium,1-(1-hexyl)-2,3-dimethylimidazolium,1-(1-octyl)-2,3-di-methylimidazolium, 3-butylimidazolium,1,4-dimethyl-3-octylimidazolium, 1,4,5-trimethyl-3-butylimidazolium and1,4,5-trimethyl-3-octylimidazolium.

Useful cations additionally include ions which are especially formedfrom the aforementioned cations owing to dimerization, trimerization orpolymerization to form dications, trications or polycations. These alsoinclude those dications, trications and polycations which possess apolymeric backbone, for example based on siloxanes, polyethers,polyesters, polyamides or polyacrylates, especially branched andhyperbranched polymers.

Additionally useful are conductivity additives in which the cation [A]⁺is a pyridinium ion (XIIIa) in which

one or more of the

-   R¹ to R⁵ radicals are independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-Ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R¹ to R⁵ radicals are each hydrogen or methyl or ethyl, R³    is dimethylamino and the remaining R¹, R², R⁴ and R⁵ radicals are    each hydrogen, all R¹ to R⁵ radicals are hydrogen, R² is carboxyl or    carboxamide and the remaining R¹, R², R⁴ and R⁵ radicals are each    hydrogen, or R¹ and R² or R² and R³ are 1,4-buta-1,3-dienylene and    the remaining R¹, R², R⁴ and R⁵ radicals are each hydrogen,    and especially one in which-   R¹ to R⁵ are each hydrogen, or one of the R¹ to R⁵ radicals is    methyl or ethyl and the remaining R¹ to R⁵ radicals are each    hydrogen.

Very particularly preferred pyridinium ions (XIIIa) include1-(1-hexyl)pyridinium, 1-(1-octyl)pyridinium, 1-(1-hexyl)pyridinium,1-(1-octyl)pyridinium, 1-(1-dodecyl)pyridinium,1-(1-tetradecyl)pyridinium, 1-(1-hexadecyl)pyridinium,1-(1-hexyl)-2-methylpyridinium, 1-(1-octyl)-2-methylpyridinium,1-(1-dodecyl)-2-methylpyridinium, 1-(1-tetradecyl)-2-methylpyridinium,1-(1-hexadecyl)-2-methylpyridinium, 1-(1-hexyl)-2-ethylpyridinium,1-(1-octyl)-2-ethylpyridinium, 1-(1-dodecyl)-2-ethylpyridinium,1-(1-tetradecyl)-2-ethylpyridinium, 1-(1-hexadecyl)-2-ethylpyridinium,1-(1-hexyl)-2-methyl-3-ethylpyridinium and1-(1-octyl)-2-methyl-3-ethylpyridinium,1-(1-dodecyl)-2-methyl-3-ethylpyridinium,1-(1-tetradecyl)-2-methyl-3-ethylpyridinium and1-(1-hexadecyl)-2-methyl-3-ethylpyridinium.

Additionally useful are conductivity additives in which the cation [A]⁺is a pyridazinium ion (XIIIb)

in which

-   R₁ to R₄ are each hydrogen, or one or more of the R₁ to R₄ radicals    is independently 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl),    2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl,    2-methyl-1-butyl, 3-2-methyl-2-butyl, 3-methyl-2-butyl,    2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl,    3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl,    3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl,    3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl,    3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl,    3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl,    tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl,    nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl,    pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl,    phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl,    2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl,    2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl,    2-cyclohexylethyl, 3-cyclohexylpropyl, and the remaining R₁ to R₄    radicals are each hydrogen or methyl or ethyl.

Very particular preference is given to conductivity additives in whichthe cation [A]⁺ is a pyrimidinium ion (XIIIc)

in which

-   R₁ is hydrogen, methyl or ethyl and R₂ to R₄ are each independently    hydrogen or methyl, or one or more of the R₁ to R₄ radicals is    independently 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl),    2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl,    2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl,    3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl,    2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl,    2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl,    2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl,    2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl,    2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl,    decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl,    hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl,    docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl,    octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₄ radicals are each hydrogen or methyl or ethyl.

Other useful conductivity additives are those in which the cation [A]⁺is a pyrazinium ion (XIIId)

in whichone or more of the

-   R₁ to R₄ radicals are each independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₄ radicals are each hydrogen or methyl or ethyl,-   R₁ is hydrogen, methyl or ethyl, R₂ and R₄ are each methyl and R₃ is    hydrogen,-   R₁ to R₄ are each methyl, or-   R₁ to R₄ are each methyl or hydrogen.

Further useful conductivity additives are those in which the cation [A]⁺is a pyrazolium ion (XIIIf), (XIIIg) or (XIIIg′) in which

-   R₁ is hydrogen, methyl or ethyl and-   R₂ to R₄ are each independently hydrogen or methyl, one or more of    the R₁ to R₄ radicals is independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₄ radicals are each hydrogen or methyl or ethyl.

Further useful conductivity additives are those in which the cation [A]⁺is a pyrazolium ion (XIIIh)

in whichone or more of the

-   R₁ to R₄ radicals is independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₄ radicals are each hydrogen or methyl or ethyl.

Additional useful conductivity additives are those in which the cation[A]⁺ is a 1-pyrazolinium ion (XIIIi)

in whichone or more of the

-   R₁ to R₄ radicals are independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₄ radicals are each hydrogen or methyl or ethyl.

Further useful conductivity additives are those in which the cation[A]^(+ is a) 2-pyrazolinium ion (XIIIj)

in whichone or more of the

-   R₁ to R₄ radicals are independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₄ radicals are each hydrogen or methyl or ethyl.

Useful conductivity additives are also those in which the cation [A]⁺ isa 3-pyrazolinium ion (XIIIk) or (XIIIk′)

in whichone or more of the

-   R₁ to R₄ radicals is independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₄ radicals are each hydrogen or methyl or ethyl.

Additionally useful conductivity additives are those in which the cation[A]⁺ is an imidazolinium ion (XIIIl)

in which

-   R is H or methyl,-   R₁ and R₂ are each independently hydrogen, methyl or ethyl, or a    linear saturated or unsaturated acyl radical having 14 to 22 and    preferably 16 to 18 carbon atoms, and R₃ to R₆ are each    independently hydrogen, a linear saturated alkyl radical which has 1    to 4 carbon atoms and optionally contains OH groups, preferably    methyl or a fatty acid radical; especially preferably, R₁ and R₂ are    each fatty acid acyl radicals, and R or R₂ and R₃ are each fatty    acid acyl radicals. Of particular significance are the substances of    the formula (XIIIm).-    In some cases, the literature also introduces erroneous formulae    for these (analogous to formula XIIIm′ or XIIIl).

Other useful conductivity additives are those in which the cation [A]⁺is an imidazolinium ion (XIIIm) or (XIIIm′)

in which

-   R is H or methyl,-   R₁ and R₂ are each independently hydrogen, methyl or ethyl, or a    linear saturated or unsaturated acyl radical having 14 to 22 and    preferably 16 to 18 carbon atoms, and R₃ to R₆ are each    independently hydrogen, a linear saturated alkyl radical which has 1    to 4 carbon atoms and may contain OH groups, preferably methyl or a    fatty acid radical; especially preferably R₁ and R₂ are each fatty    acid acyl radicals, and R or R₂ and R₃ are each fatty acid acyl    radicals. Of particular significance are the substances of the    formula (XIIIm). In some cases, the literature also introduces    erroneous formulae for these (analogous to formula XIIIm′ or XIIIl).

Additional useful conductivity additives are those in which the cation[A]⁺ is a thiazolium ion (XIIIo) or (XIIIo′), or else is an oxazoliumion (XIIIp),

in whichone or more of the

-   R₁ to R₃ radicals is independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₄ radicals are each hydrogen or methyl or ethyl.

Also useful are conductivity additives in which the cation [A]⁺ is a1,2,4-triazolium ion (XIIIq), (XIIIq′) or (XIIIq″)

in whichone or more of the

-   R₁ to R₃ radicals is independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₄ radicals are each hydrogen or methyl or ethyl.

Further useful conductivity additives are those in which the cation [A]⁺is a 1,2,3-triazolium ion (XIIIr), (XIIIr′) or (XIIIr″)

in which

-   R₁ is hydrogen, methyl or ethyl and-   R₂ and R₃ are each independently hydrogen or methyl, or R₂ and R₃    together are 1,4-buta-1,3-dienylene, one or more of the R₁ to R₃    radicals is independently 1-butyl, 2-butyl, 2-methyl-1-propyl    (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl,    3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl,    3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl,    2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl,    2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl,    2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl,    2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl,    2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl,    decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl,    hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl,    docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl,    octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₃ radicals are each hydrogen or methyl or ethyl.

Additionally useful conductivity additives are those in which the cation[A]⁺ is a pyrrolidinium ion (XIIIs)

in which

-   R₁ is hydrogen, methyl, ethyl or phenyl and-   R₂ to R₉ are each independently hydrogen or methyl, one or more of    the R₁ to R₃ radicals is independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₃ radicals are each hydrogen or methyl or ethyl.

Additional useful conductivity additives are those in which the cation[A]⁺ is an imidazolidinium ion (XIIIt)

in whichone or more of the

-   R₁ to R₈ radicals is independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining radicals R₁ to R₈ are each hydrogen or methyl or ethyl.

Also useful are conductivity additives in which the cation [A]⁺ is anammonium ion (IV)

in whichone or more of the

-   R₁ to R₃ radicals are independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₄ radicals are each hydrogen or methyl or ethyl; or    R₁ to R₃ are each independently hydrogen or C₁-C₁₈-alkyl and R₄ is    2-hydroxyethyl; or R₁ and R₂ together are 1,5-pentylene or    3-oxa-1,5-pentylene and R₃ is alkyl, 2-hydroxyethyl or 2-cyanoethyl.

Additionally useful conductivity additives are those in which the cation[A]⁺ is a guanidinium ion (IVv)

in whichone or more of the

-   R₁ to R₅ radicals is independently 1-butyl, 2-butyl,    2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl),    1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl,    2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl,    2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,    4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,    4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,    2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,    2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl,    octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,    pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl,    heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl,    heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),    diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,    cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,    cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, and the    remaining R₁ to R₄ radicals are each hydrogen or methyl or ethyl; R₁    to R₅ are each independently C₁-C₁₈-alkyl; or R₁ to R₅ are    independently hydrogen or C₁-C₁₈-alkyl or 2-hydroxyethyl.

Useful conductivity additives are also those in which the cation [A]⁺ isa derivative of an ethanolamine, for example a cholinium ion (XIIIw), orof a diethanolamine (XIIIw′), or of a triethanolamine (XIIIw″),

-   R₁ and R₂ are each independently methyl, ethyl, 1-butyl or 1-octyl    and R₃ is hydrogen, methyl, ethyl, acetyl, —SO₂OH or —PO(OH)₂; R₁ is    methyl, ethyl, 1-butyl or 1-octyl, R₂ is a —CH₂—CH₂—OR₄— group and    R₃ and R₄ are each independently hydrogen, methyl, ethyl, acetyl,    —SO₂OH or —PO(OH)₂; or R₁ is a —CH₂—CH₂—OR₄— group, R₂ is a    —CH₂—CH₂—OR₅— group, and R₃ to R₅ are each independently hydrogen,    methyl, ethyl, acetyl, —SO₂OH or —PO(OH)₂; R₁ is methyl, ethyl,    1-butyl, 1-octyl, acetyl; —SO₂OH, or —PO(OH)₂, and R₃ to R₅ are each    independently hydrogen, methyl, ethyl, acetyl, —SO₂OH, —PO(OH)₂, or    —(C_(n)H_(2n)O)_(m)R₁ where n=1 to 5 and m=1 to 100.

Preference is also given to compounds in which R, R₁ and R₂ are eachalkyl groups having 1 to 4 carbon atoms, more preferably each a methylgroup, and R₃ and/or R₄ are saturated or unsaturated fatty acid or acylradicals having 8 to 22 carbon atoms, preferably 12 to 18 carbon atoms.It is also possible for mixtures of the acyl or fatty acid radicals(especially, for example, in naturally occurring ratios) to be present.

Very particular preference is given to the formula (XIIIw″) where R, R₁,R₂ are each an alkyl radical having 1 to 4 carbon atoms, especiallymethyl groups, and R₃ is a fatty acid radical and R₄ and R₅ are each afatty acid radical or hydrogen.

Useful conductivity additives are those in which the cation [A]⁺ is aphosphonium ion (VI) in which R₁ to R₃ are each independentlyC₁-C₁₈-alkyl, especially butyl, isobutyl, 1-hexyl or 1-octyl.

Particular preference is given to the tributyloctylphosphonium,triisobutyloctylphosphonium, trioctylethylphosphonium,trioctylbutylphosphonium, tributylhexylphosphonium,tetraoctylphosphonium, tributyltetradecylphosphonium,trihexyloctylphosphonium, trihexyltetradecylphosphonium, and thetetratetradecylphosphonium cation.

The conductivity additives used in accordance with the invention consistof at least one of the aforementioned cations combined with in each caseat least one anion. Useful anions are in principle all anions which, inconjunction with the cation, lead to a liquid which forms a clearsolution in the nonaqueous hydraulic oil.

The anion [Y]^(n−) of the conductivity additives is, for example,selected from:

-   -   the group of the halides and halogenated compounds of the        formulae: F⁻ Cl⁻, Br⁻, I⁻, BF₄ ⁻, PF₆ ⁻, AlCl₄ ⁻, Al₂Cl₇ ⁻,        Al₃Cl₁₀ ⁻, AlBr₄ ⁻, FeCI₄ ⁻, BCl₄ ⁻ SbF₆ ⁻, AsF₆ ⁻, ZnCl₃ ⁻,        SnCl₃ ⁻, CuCl₂ ⁻, CF₃SO₃ ⁻, (CF₃SO₃)₂N⁻, CF₃CO₂ ⁻, CCl₃CO₂ ⁻,        CN⁻, SCN⁻, OCN⁻, NO₂ ⁻, NO₃ ⁻, N(CN)⁻;    -   the group of the sulphates, sulphites and sulphonates of the        general formulae: SO₄ ²⁻, HSO₄ ⁻, SO₃ ^(2″), HSO₃ ⁻, R^(a)OSO₃        ⁻, R^(a)SO₃ ⁻;    -   the group of the phosphates of the general formulae: PO₄ ³⁻,        HPO₄ ²⁻, H₂PO⁴⁻, R^(a)PO₄ ²⁻, HR^(a)PO⁴⁻, R^(a)R^(b)PO⁴⁻; p1 the        group of the phosphonates and phosphinates of the general        formula: R^(a)HPO₃ ⁻, R^(a)R^(b)PO₂ ⁻, R^(a)R^(b)PO₃ ⁻;    -   the group of the phosphites of the general formulae: PO₃ ³⁻,        HPO₃ ²⁻, H₂PO₃ ⁻, R^(a)PO₃ ²⁻, R^(a)HPO₃ ⁻, R^(a)R^(b)PO₃ ⁻;    -   the group of the phosphonites and phosphinites of the general        formula: R^(a)R^(b)PO₂ ⁻, R^(a)HPO₂ ⁻, R^(a)R^(b)PO⁻, R^(a)HPO⁻;    -   the group of the carboxylates of the general formulae:        R^(a)COO⁻;    -   the group of the borates of the general formulae: BO₃ ³⁻, HBO₃        ²⁻, H₂BO₃ ⁻, R^(a)R^(b)BO₃ ⁻, R^(a)HBO₃ ⁻, R^(a)BO₃ ²⁻,        B(OR^(a))(OR^(b))(OR^(c))(OR^(d))⁻, B(HSO₄)⁻, B(R^(a)SO₄)⁻;    -   the group of the boronates of the general formulae: R^(a)BO₂ ²⁻,        R^(a)R^(b)BO⁻;    -   the group of the carbonates and carbonic esters of the general        formulae: HCO₃ ⁻, CO₃ ²⁻, R^(a)CO₃ ⁻;    -   the group of the silicates and silicic esters of the general        formulae: SiO₄ ⁴⁻, HSiO₄ ³⁻, H₂SiO₄ ²⁻, H₃SiO₄ ⁻, R^(a)SiO₄ ³⁻,        R^(a)R^(b)SiO₄ ²−, R^(a)R^(b)R^(c)SiO₄ ⁻, HR^(a)SiO₄ ²⁻,        H₂R^(a)SiO₄ ⁻, HR^(a)R^(b)SiO₄ ⁻;    -   the group of the alkyl- and arylsilane salts of the general        formulae: R^(a)SiO₃ ³⁻, R^(a)R^(b)SiO₂ ²⁻, R^(a)R^(b)R^(c)SiO⁻,        R^(a)R^(b)R^(c)SiO₃ ⁻, R^(a)R^(b)R^(c)SiO₂ ⁻, R^(a)R^(b)SiO₃ ²⁻;    -   the group of the carboximides, bis(sulphonyl)imides and        sulphonylimides of the general formulae:

-   -   the group of the methides of the general formula:

-   -   the group of the alkoxides and aryl oxides of the general        formula: R^(a)O⁻;    -   the group of the halometallates of the general formula        [M_(r)Hal_(t)]^(s−) where M is a metal and Hal is fluorine,        chlorine, bromine or iodine, r and t are positive integers and        specify the stoichiometry of the complex and s is a positive        integer and specifies the charge of the complex;    -   the group of the sulphides, hydrogensulphides, polysulphides,        hydrogenpolysulphides and thiolates of the general formulae:    -   S²⁻, HS⁻, [S_(v)]²⁻, [HS_(v)]⁻, [R^(a)S]⁻, where v is a positive        integer of 2 to 10;    -   the group of the complex metal ions such as Fe(CN)₆ ³⁻, Fe(CN)₆        ⁴⁻, MnO₄ ⁻, Fe(CO)₄ ⁻.

In these formulae, R^(a), R^(b), R^(c) and R^(d) are each independently

-   -   hydrogen;    -   C₁-C₃₀-alkyl and the aryl-, heteroaryl-, cycloalkyl-, halogen-,        hydroxyl-, amino-, carboxyl-, formyl-, —O—, —CO—, —CO—O— or        —CO—N<-substituted components thereof, for example methyl,        ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methyl-1-propyl        (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl,        3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl,        3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl,        3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,        4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,        4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl,        2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl,        3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl,        3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl,        dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl,        heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl,        tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl,        octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl),        diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl,        cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl,        cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl,        methoxy, ethoxy, formyl, acetyl or C_(q)F_(2(q-a)+(1-b))H_(2a+b)        where q<30, 0≦a≦q and b=0 or 1 (for example CF₃, C₂F₅,        CH₂CH₂—C_((q-2))F_(2(q-2)+1), C₆F₁₃, C₈F₁₇, C₁₀F₂₁, C₁₂F₂₅);    -   C₃-C₁₂-cycloalkyl and the aryl-, heteroaryl-, cycloalkyl-,        halogen-, hydroxyl-, amino-, carboxyl-, formyl-, —O—, —CO— or        —CO—O-substituted components thereof, for example cyclopentyl,        2-methyl-1-cyclopentyl, 3-methyl-1-cyclopentyl, cyclohexyl,        2-methyl-1-cyclohexyl, 3-methyl-1-cyclohexyl,        4-methyl-1-cyclohexyl or C_(q)F_(2(q-a)−(1-b))H_(2a−b) where        q≦30, 0≦a≦q and b=0 or 1;    -   C₂-C₃₀-alkenyl and the aryl-, heteroaryl-, cycloalkyl-,        halogen-, hydroxyl-, amino-, carboxyl-, formyl-, —O—, —CO— or        —CO—O-substituted components thereof, for example 2-propenyl,        3-butenyl, cis-2-butenyl, trans-2-butenyl or        C₁F_(2(q-a)−(1-b))H_(2a−b) where q≦30, 0≦a≦q and b=0 or 1;    -   C₃-C₁₂-cycloalkenyl and the aryl-, heteroaryl-, cycloalkyl-,        halogen-, hydroxyl-, amino-, carboxyl-, formyl-, —O—, —CO— or        —CO—O-substituted components thereof, for example        3-cyclopentenyl, 2-cyclohexenyl, 3-cyclohexenyl,        2,5-cyclohexadienyl or C_(q)F_(2(q-a)−3(1-b))H_(2a−3b) where        q≦30, 0≦a≦q and b=0 or 1;    -   aryl or heteroaryl having from 2 to 30 carbon atoms and the        alkyl-, aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxyl-,        amino-, carboxyl-, formyl-, —O—, —CO— or —CO—O-substituted        components thereof, for example phenyl, 2-methylphenyl        (2-tolyl), 3-methylphenyl (3-tolyl), 4-methylphenyl,        2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl,        2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl,        3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-phenylphenyl,        1-naphthyl, 2-naphthyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl,        2-pyridinyl, 3-pyridinyl, 4-pyridinyl or C₆F_((5-a))H_(a) where        0≦a≦5; or    -   two radicals are an unsaturated, saturated or aromatic ring        which is optionally substituted by functional groups, aryl,        alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or        heterocycles and optionally interrupted by one or more oxygen        and/or sulphur atoms and/or one or more substituted or        unsubstituted imino groups.

Useful anions are, for example, chloride; bromide; iodide; thiocyanate;hexafluorophosphate; trifluoromethanesulphonate; methanesulphonate;formate; acetate; glycolate; lactate; oxalate; citrate; malate; maleate;tartrate; mandelate; nitrate; nitrite; trifluoroacetate; sulphate;hydrogensulphate; methylsulphate; ethylsulphate; 1-propylsulphate;1-butylsulphate; 1-hexylsulphate; 1-octylsulphate; phosphate;dihydrogenphosphate; hydrogenphosphate; C₁-C₄-dialkylphosphates;propionate; tetrachloroaluminate; Al₂Cl₇ ⁻; chlorozincate;chloroferrate; bis(trifluoromethylsulphonyl)imide;bis(pentafluoroethylsulphonyl)imide; bis(methylsulphonyl)imide;bis(p-tolylsulphonyl)imide; tris(trifluoromethylsulphonyl)methide;bis(pentafluoroethylsulphonyl)methide; p-tolylsulphonate;tetracarbonylcobaltate; dimethyleneglycolmonomethylethersulphate;oleate; stearate; acrylate; methacrylate; hydrogencitrate;vinylphosphonate; bis(pentafluoroethyl)phosphinate; borates such asbis[salicylato(2-)]borate, bis[oxalato(2-)]borate,bis[1,2-benzenediolato(2-)-O,O′]borate, tetracyanoborate,tetrafluoroborate; dicyanamide;tris(pentafluoroethyl)trifluorophosphate;tris(heptafluoropropyl)trifluorophosphate, cyclic arylphosphates such aspyrocatecholphosphate (C₆H₄O₂)P(O)O⁻ and chlorocobaltate.

Preferred anions are selected from the group of—without any claim tocompleteness—the halides, bis(perfluoroalkylsulphonyl)amides and-imides, for example bis(trifluoromethylylsulphonyl)imide, alkyl- andaryltosylates, perfluoroalkyltosylates, nitrate, sulphate,hydrogensulphate, alkyl- and arylsulphates, polyethersulphates and-sulphonates, perfluoroalkylsulphates, sulphonate, alkyl- andarylsulphonates, perfluorinated alkyl- and arylsulphonates, alkyl- andarylcarboxylates, perfluoroalkylcarboxylates, perchlorate,tetrachloroaluminate, saccharinate. Also preferred are dicyanamide,thiocyanate, isothiocyanate, tetraphenylborate,tetrakis(pentafluorophenyl)borate, tetrafluoroborate,hexafluorophosphate, polyetherphosphates, dialkylphosphates,isostearates, alkylbenzylsulphonates, bis(alkyl)phosphinates,phosphatides, decanoates and phosphate.

Very particularly preferred anions are: chloride, bromide,hydrogensulphate, tetrachloroaluminate, thiocyanate, methylsulphate,ethyl sulphate, methanesulphonate, formate, acetate, glycolate, lactate,dimethylphosphate, diethylphosphate, p-tolylsulphonate,tetrafluoroborate, hexafluorophosphate, diethylphosphate, isostearate,dodecylbenzylsulphonate, bis(2,4,4-trimethylpentyl)phosphinate,phosphatide, decanoate, and tosylate.

According to the invention, in a further preferred embodiment, thoseconductivity additives or mixtures thereof are used which comprise acombination of a 1,3-dialkylimidazolium, 1,2,3-trialkylimidazolium,1,3-dialkylimidazolinium and 1,2,3-trialkylimidazolinium cation with ananion selected from the group of the halides,bis(trifluoromethylylsulphonyl)imide, perfluoroalkyltosylates,alkylsulphates and -sulphonates, perfluorinated alkylsulphonates and-sulphates, perfluoroalkylcarboxylates, perchlorate, dicyanamide,thiocyanate, isothiocyanate, tetraphenylborate,tetrakis(pentafluorophenyl)borate, tetrafluoroborate,hexafluorophosphate, acetate, glycolate, lactate.

The mixing ratios of hydraulic oil and conductivity additive are between100 000:1 and 10:1, preferably between 10 000:1 and 20:1, morepreferably 5000:1 and 25:1, most preferably between 1000:1 and 50:1 (allratios are % by weight)

The composition composed of hydraulic oil and conductivity additive maycomprise further customary additives. These include, for example,viscosity index improvers, defoamers, pour point depressants, extremepressure additives, anti-wear additives, corrosion inhibitors, frictionmodifier additives, demulsifying additives, antioxidants or detergents.

The minimum conductivity required is, for example, for applications incold store hydraulic fluids, at least 1000 pS/m. The desiredconductivity is significantly higher, but cannot be achieved in alasting manner by the conductivity improvers known to date, since thevolatile solvent evaporates and there are associated precipitations ofsalts or other substances. In any case, no upper limit in theconductivity is needed, since the desired action, the tendency to staticdischarge, decreases ever further with rising conductivity. Theinventive ionic conductivity additives with organic radicals in the ionsdo not have these disadvantages. In other fields of use, the minimumconductivities and desired conductivities may differ, and maximumconductivities may also be relevant.

The inventive conductivity additives and the use thereof will bedescribed below by way of example, without any possibility that theinvention can be considered as restricted to these illustrativeembodiments. Where ranges, general formulae or compound classes arespecified hereinafter, these shall encompass not just the correspondingranges or groups of compounds which are mentioned explicitly, but alsoall subranges and subgroups of compounds which can be obtained byselection of individual values (ranges) or compounds.

WORKING EXAMPLES

The present invention is described by way of example in the examplesadduced below, without any possibility that the invention, whose scopeof protection is evident from the overall description and the claims,can be read as being restricted to the embodiments specified in theexamples.

Experimental Procedure:

100 g of Kühlhaus 50468783 hydraulic oil (from Jungheinrich) wereinitially charged and in each case 1 g or 5 g of the conductivityadditive were weighed in. The sample was stirred until it washomogeneous and then the electrical conductivity at rest and theturbidity value FNU (formazine nephelometric units) were determined.

The conductivity at rest was determined to DIN 51412 part 1 (2005-06).

To determine the opacity, a NEPHLA LPG239 laboratory turbidityphotometer (manufacturer: Dr. Bruno Lange GmbH, Dusseldorf) was used.The standard used was DIN standard formazine.

The turbidity value was used to quantitatively detect the qualitativephenomenon of turbidity. The aim of the turbidity measurement is toobtain statements about the content of scattering particles. FNU (alsoFTU: formazine turbidity unit) is a unit of measurement of turbidityused according to standard ISO 7027, which was measured with scatteredlight. In order to make scattered light measurements comparable, theseinstruments were calibrated with a suspension, for example formazine, inorder to be able to reference the measurements to a common standard.

Procedure of the Turbidity Measurement:

The measurement cuvette was filled with the particular sample up to theblack ring and conditioned to the appropriate temperature (in each case0° C. and room temperature). Thereafter, the cuvette was placed into theapparatus. At least 3 measurements were carried out in different cuvettepositions, and the mean was calculated. To prevent condensation ofatmospheric moisture, the conditions employed were 0° C. in protectivegas atmosphere.

TABLE 1 Turbidity and conductivity at rest at room temperature ofadditized hydraulic oil (Kühlhaus 50468783 hydraulic oil (fromJungheinrich)) Conductivity at Turbidity rest value pS/m FNU blankvalue, pure    50 0.24 hydraulic oil 1% addition of  38 520 2.7trihexyltetradecyl- phosphonium bis(2,4,4- trimethylpentyl)phosphinate5% addition of 210 000 trihexyltetradecyl- phosphonium bis(2,4,4-trimethylpentyl)phosphinate 1% addition of  50 000 0.24 TEGO ® IL ZTO 5%addition of 281 700 0.24 TEGO ® IL ZTO TEGO ® IL ZTO, a fatty acid aminepolyglycol ether diester quat, CAS No. 217813-30-4, but also with TEGO ®IL ZTI, a talloylamine polyglycol ether diester quat, and with TEGO ® ILIM36, a 2-(C₁₇ and C₁₇-unsaturated alkyl)-1-[2-(C₁₈ and C₁₈-unsatd.amido)ethyl]-4,5-dihydro-1-methylimidazolium methylsulphate andtrihexyltetradecyl-phosphonium bis(2,4,4-trimethylpentyl)phosphinate,show high conductivities coupled with very low turbidity values achieved(TEGO ® is a trademark of Evonik Goldschmidt GmbH.

Even at temperatures around freezing point (0° C.), the organicconductivity improver remains in solution and hence the high relativeconductivity is maintained. These conductivities are significantlyhigher compared to an inorganic conductive salt in maximum concentration(i.e. with sediment).

The results show clearly that the inventive formulations can be equippedwith a much higher proportion of conductivity additive compared toindustrial solutions used to date. Higher absolute values for theconductivity are thus also achievable and establishable compared to theprior art.

Having thus described in detail various embodiments of the presentinvention, it is to be understood that the invention defined by theabove paragraphs is not to be limited to particular details set forth inthe above description as many apparent variations thereof are possiblewithout departing from the spirit or scope of the present invention.

1. Composition comprising nonaqueous hydraulic oils or lubricants andone or more conductivity additives which form clear solutions ormixtures with the hydraulic oil and optionally further customaryadditives.
 2. Composition according to claim 1, characterized in thatthe conductivity additive is liquid and of ionic structure and containsions with organic radicals.
 3. Composition according to claim 1,characterized in that the ionic conductivity additive comprises at leastone cation and/or one anion with organic radicals.
 4. Compositionaccording to claim 1, characterized in that the ionic conductivityadditive in the cation and/or anion contains at least one organicradical with at least 8 carbon atoms, where the sum of the carbon atomsof all radicals is at least
 14. 5. Composition according to claim 1,comprising, as a conductivity additive, a compound of the formulae (I),(II) or (III)[A]_(n) ⁺[Y]^(n−)  (I) in which n is 1, 2, 3 or 4, [A]⁺ is a quaternaryammonium cation, an oxonium cation, a sulphonium cation or a phosphoniumcation and [Y]^(n−) is an n-valent anion and/or mixed salts of thegeneral formulae (II)[A¹]⁺[A²]⁺[Y]²⁻  (IIa),[A¹]⁺[A²]⁺[A³]⁺[Y]³⁻  (IIb), or[A¹]⁺[A²]⁺[A³]⁺[A⁴]^(+[Y]) ⁴⁻  (IIc), where [A¹]⁺, [A²]⁺ [A³]⁺ and [A⁴]⁺are each independently selected from the groups specified for [A]⁺,[Y]^(n−) is as defined for formula (I) and/or mixed salts of the generalformulae (III)[A¹]⁺[A²]⁺[A³]⁺[M¹]⁺[Y]⁴⁻  (IIIa),[A¹]⁺[A²]⁺[M¹]⁺[M²]⁺[Y]⁴⁻  (IIIb),[A¹]⁺[M¹]⁺[M²]⁺[M³]⁺[Y]⁴⁻  (IIIc),[A¹]⁺[A²]⁺[M¹]⁺[Y]³⁻  (IIId),[A¹]⁺[M¹]⁺[M²]⁺[Y]³⁻  (IIIe),[A¹]⁺[M¹]⁺[Y]²⁻  (IIIf),[A¹]⁺[A²]+[M⁴]²⁺[Y]⁴⁻  (IIIg),[A¹]⁺[M¹]⁺[M⁴]²⁺[Y]⁴⁻  (IIIh),[A¹]⁺[M⁵]³⁺[Y]⁴⁻  (IIIi), or[A¹]⁺[M⁴]²⁺[Y]³⁻  (IIIj), where [A¹]⁺, [A²]⁺ or [A³]⁺ are eachindependently selected from the groups specified for [A]⁺, [Y]^(n−) isas defined for formula (I) and [M¹]⁺, [M²]⁺, [M³]⁺ are each monovalentmetal cations, [M⁴]²⁺ are divalent metal cations and [M⁵]³⁺ aretrivalent metal cations or mixtures of all formulae (I) to (III). 6.Composition according to claim 5 comprising, as a cation [A⁺],structural elements of the general formulae (IV) to (VIII)R¹R²R³R⁴N⁺  (IV)R¹R²N⁺═CR³R⁴  (V)R¹R²R³R⁴P⁺  (VI)R¹R²P⁺═CR³R⁴  (VII)R¹R²R³S⁺  (VIII) in which R¹, R², R³, R⁴ are the same or different andare each hydrogen, a linear or branched aliphatic hydrocarbon radicalwhich has 1 to 30 carbon atoms and may contain double bonds, with theproviso that at least one radical is not hydrogen, a cycloaliphatichydrocarbon radical which has 5 to 40 carbon atoms and may containdouble bonds, an aromatic hydrocarbon radical having 6 to 40 carbonatoms, an alkylaryl radical having 7 to 40 carbon atoms, a linear orbranched aliphatic hydrocarbon radical which has 2 to 30 carbon atoms,may contain double bonds and is interrupted by one or more heteroatomssuch as oxygen, NH, NR′ where R′ is a C₁-C₃₀-alkyl radical which maycontain double bonds, a linear or branched aliphatic hydrocarbon radicalwhich has 2 to 30 carbon atoms, may contain double bonds and isinterrupted by one or more functionalities selected from the group of—O—C(O)—, —(O)C—O—, —NH—C(O)—, —(O)C—NH, —(CH₃)N—C(O)—, —(O)C—N(CH₃)—,—S(O₂)—O—, —O—S(O₂)—, —S(O₂)—NH—, —NH—S(O₂)—, —S(O₂)—N(CH₃)—,—N(CH₃)—S(O₂)—, a linear or branched aliphatic or cycloaliphatichydrocarbon radical which has 1 to 30 carbon atoms, may contain doublebonds and is functionalized terminally with OH, OR′, NH₂, N(H)R′, N(R′)₂in which R′ is a C₁-C₃₀-alkyl radical which may contain double bonds, ora polyether of blockwise or random construction according to—(R⁵—O)_(n)—R⁶, where R⁵ is a linear or branched hydrocarbon radicalcontaining 2 to 4 carbon atoms, n is 1 to 100 and R⁶ is hydrogen, alinear or branched aliphatic hydrocarbon radical which has 1 to 30carbon atoms and may contain double bonds, a cycloaliphatic hydrocarbonradical which has 5 to 40 carbon atoms and may contain double bonds, anaromatic hydrocarbon radical having 6 to 40 carbon atoms, an alkylarylradical having 7 to 40 carbon atoms or a —C(O)—R⁷ radical where R⁷ is alinear or branched aliphatic hydrocarbon radical which has 1 to 30carbon atoms and may contain double bonds, a cycloaliphatic hydrocarbonradical which has 5 to 40 carbon atoms and may contain double bonds, anaromatic hydrocarbon radical having 6 to 40 carbon atoms, an alkylarylradical having 7 to 40 carbon atoms.
 7. Composition according to claim6, characterized in that the metal cations [M¹]⁺, [M²]⁺, [M³]⁺, [M⁴]²⁺and [M⁵]³⁺ are selected from the metal cations of groups 1, 2, 6, 7, 8,9, 10, 11, 12 and 13 of the Periodic Table in the IUPAC nomenclature. 8.Composition according to claim 7, characterized in that the anions[Y]^(n−) are selected from the group of the halides, carboxylates,phosphates, thiocyanates, isothiocyanates, dicyanamides, sulphates,alkylsulphates, sulphonates, alkylsulphonates, tetrafluoroborate,hexafluoro-phosphate, bis(trifluoromethylsulphonyl)imide,dialkylphosphates, isostearates, alkylbenzylsulphonates,bis(alkyl)phosphinates, phosphatides, decanoates.
 9. Compositionaccording to claim 5, characterized in that the anions [Y]^(n−) arecombined with cations [A¹]⁺, [A^(2]) ⁺ [A³]⁺ and [A⁴]⁺ in the form ofsubstituted ammonium, phosphonium, pyridinium or imidazolium cations.10. Composition according to claim 9, characterized in that theconductivity additive or the mixture of conductivity additives iscomposed of at least one quaternary nitrogen and/or phosphorus compoundand/or sulphur compound and at least one anion [Y]^(n−) and the meltingpoint of the composition is below about +250° C.
 11. Compositionaccording to claim 10, characterized in that the conductivity additiveor mixtures thereof is/are liquid at room temperature.
 12. A method ofincreasing the electrical conductivity in hydraulic and/or lubricantsystem which comprises of adding an effective amount of the compositionof claim 1 to a hydraulic and/or lubricant system.
 13. The method ofclaim 12, wherein the one or more hydraulic oils or lubricants compriseof one or more compounds selected fromN,N-di(tallowyloxyethyl)-N,N-dimethylammonium chloride;N,N-di(canolyloxyethyl)-N,N-dimethylammonium chloride;N,N-di(tallowyloxyethyl)-N-methyl,N-(2-hydroxyethyl)ammoniummethylsulphate; N,N-di(canolyloxyethyl)-N-methyl,N-(2-hydroxyethyl)ammonium methylsulphate;N,N-di(tallowylamidoethyl)-N-methyl,N-(2-hydroxyethyl)ammoniummethylsulphate; N,N-di(2-tallowyloxy-2-oxo-ethyl)-N,N-dimethylammoniumchloride; N,N-di(2-canolyloxy-2-oxo-ethyl)-N,N-dimethylammoniumchloride;N,N-di(2-tallowyloxyethylcarbonyloxyethyl)-N,N-dimethylammoniumchloride; N,N-di(2-canolyloxyethylcarbonyloxyethyl)-N,N-dimethylammoniumchloride;N(2-tallowoyloxy-2-ethyl)-N-(2-tallowyloxy-2-oxo-ethyl)-N,N-dimethylammoniumchloride;N(2-canolyloxy-2-ethyl)-N(2-canolyloxy-2-oxo-ethyl)-N,N-dimethylammoniumchloride; N,N,N-tri(tallowyloxyethyl)-N-methylammonium chloride;N,N,N-tri(canolyloxyethyl)-N-methylammonium chloride;1,2-ditallowyloxy-3-N,N,N-trimethylammoniopropyl chloride,1,2-dicanolyloxy-3-N,N,N-trimethylammoniopropyl chloride,ditallowdimethylammonium chloride, ditallowdimethylammoniummethylsulphate, dimethylammonium chloride of di(hydrogenated tallow)distearyldimethylammonium chloride and/or dibehenyldimethylammoniumchloride as a conductivity additive, in hydraulic systems or lubricantsystems.
 14. The method of claim 12, wherein the composition furthercomprises as a conductivity additive, compounds which contain, ascations, structure fragmente which derive from saturated or unsaturatedcyclic compounds and from aromatic compounds having in each case atleast one trivalent nitrogen atom in a 4- to 10-membered, which mayoptionally be substituted, in hydraulic systems or lubricant systems.15. The method of claim 14, wherein the cation of the conductivityadditive has the structure of the formulae (IX), (X) and (XI), where theheterocyclic rings may optionally also contain a plurality ofheteroatoms, such as nitrogen, oxygen or sulphur, and

R¹ and R² are the same or different; R¹,R² are the same or differentwith the proviso that at least one radical is not hydrogen, and are eachhydrogen, a linear or branched aliphatic hydrocarbon radical which has 1to 30 carbon atoms and may contain double bonds, a cycloaliphatichydrocarbon radical which has 5 to 40 carbon atoms and may containdouble bonds, an aromatic hydrocarbon radical having 6 to 40 carbonatoms, an alkylaryl radical having to 40 carbon atoms, a linear orbranched aliphatic hydrocarbon radical which has 2 to 30 carbon atoms,may contain double bonds and is interrupted by one or more heteroatoms(oxygen, NH, NR′ where R′ is a C₁-C₃₀-alkyl radical which may containdouble bonds, especially —CH₃), a linear or branched aliphatichydrocarbon radical which has 2 to 30 carbon atoms, may contain doublebonds and is interrupted by one or more functionalities selected fromthe group of —O—C(O)—, —(O)C—O—, —NH—C(O)—, —(O)C—NH, —(CH₃)N—C(O)—,—(O)C—N(CH₃)—, —S(O₂)—O—, —O—S (O₂)—, —S(O₂) —NH—, —NH—S(O₂)—,—S(O₂)—N(CH₃)—, —N(CH₂)—S(O₂)—, a linear or branched aliphatic orcycloaliphatic hydrocarbon radical which has 1 to 30 carbon atoms, maycontain double bonds and is functionalized terminally with OH, OR′, NH₂,N(H)R′, N(R′)₂ in which R′ is a C₁-C₃₀-alkyl radical which may containdouble bonds, or a polyether of blockwise or random constructionaccording to —(R⁵—O)_(n)—R⁶, where R⁵ is a linear or branchedhydrocarbon radical containing 2 to 4 carbon atoms, n is 1 to 100,preferably 2 to 60, and R⁶ is hydrogen, a linear or branched aliphatichydrocarbon radical which has 1 to 30 carbon atoms and may containdouble bonds, a cycloaliphatic hydrocarbon radical which has 5 to 40carbon atoms and may contain double bonds, an aromatic hydrocarbonradical having 6 to 40 carbon atoms, an alkylaryl radical having 7 to 40carbon atoms or a —C(O)—R⁷ radical where R⁷ is a linear or branchedaliphatic hydrocarbon radical which has 1 to 30 carbon atoms and maycontain double bonds, a cycloaliphatic hydrocarbon radical which has 5to 40 carbon atoms and may contain double bonds, an aromatic hydrocarbonradical having 6 to 40 carbon atoms, an alkylaryl radical having 7 to 40carbon atoms. R is a hydrogen, a linear or branched aliphatichydrocarbon radical which has 1 to 30 carbon atoms and may containdouble bonds, a cycloaliphatic hydrocarbon radical which has 5 to 40carbon atoms and may contain double bonds, an aromatic hydrocarbonradical having 6 to 40 carbon atoms or an alkylaryl radical having 7 to40 carbon atoms, and X is an oxygen atom, a sulphur atom or asubstituted nitrogen atom (X=O, S, NR′) and the cyclic nitrogencompounds may be unsubstituted (R=H), monosubstituted or elsepolysubstituted by the R radical, where, in the case of polysubstitutionby R, the individual R radicals may be the same or different, inhydraulic systems or lubricant systems.
 16. The method of claim 14,wherein the cations of the conductivity additive can be derived fromsaturated acyclic, saturated or unsaturated cyclic compounds and fromaromatic compounds having in each case more than one trivalent nitrogenatom in a 4- to 10-membered, heterocyclic ring and may be substitutedboth on the carbon atoms and on the nitrogen atoms and may optionally befused by substituted benzene rings and/or cyclohexane rings to formpolycyclic structures, in hydraulic systems or lubricant systems.